Processes Patents (Class 562/856)
  • Patent number: 11267830
    Abstract: The present disclosure provides a complex having a metal and ligand anionic complex that is counterbalanced by a cation. The complex can be suited for many uses including in a battery.
    Type: Grant
    Filed: March 7, 2018
    Date of Patent: March 8, 2022
    Assignee: University of Massachusetts
    Inventors: Patrick J. Cappillino, Ertan Agar, Haobo Huang
  • Patent number: 8455674
    Abstract: The present invention relates to a process for producing chlorothioformate comprising reacting an alkenyl mercaptan with phosgene in a reactor in the presence of a carboxylic acid amide in an organic solvent, characterized in that the carboxylic acid amide is preliminary charged to the reactor in an amount of 10 to 50% by weight based on the whole amount of the carboxylic acid amide, and subsequently, the compound of the formula (I), phosgene and the remaining carboxylic acid amide are charged to the reactor.
    Type: Grant
    Filed: December 18, 2009
    Date of Patent: June 4, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toshiaki Suzuki, Fumi Yonehara
  • Publication number: 20110105792
    Abstract: A process for producing allyl acetate is disclosed. The process comprises reacting propylene, acetic acid, and oxygen in the presence of a supported palladium catalyst in an adiabatic reactor.
    Type: Application
    Filed: October 30, 2009
    Publication date: May 5, 2011
    Inventors: Gary A. Sawyer, Shaw-Chan Lin, Elizabeth I. Ross-Medgaarden, Andrew P. Kahn
  • Patent number: 7728171
    Abstract: A process for the preparation of acid halides of formula I which are useful as intermediates in the preparation of i.a. pharmaceutically active compounds.
    Type: Grant
    Filed: August 25, 2008
    Date of Patent: June 1, 2010
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Ursula Hoffmann, Goesta Rimmler
  • Publication number: 20100099912
    Abstract: The present invention concerns a new efficient method for the selective transformation, under mild conditions and in aqueous medium, of gaseous (ethane, propane and n-butane) and liquid (n-pentane, n-hexane, cyclopentane and cyclohexane) alkanes into carboxylic acids bearing one more carbon atom, characterized by a single-pot low-temperature (25-60° C.) reaction of the alkane with carbon monoxide in water/acetonitrile liquid medium, either in the absence or in the presence of a metal catalyst, in systems containing also an oxidant (a peroxodisulphate salt).
    Type: Application
    Filed: January 17, 2008
    Publication date: April 22, 2010
    Inventors: Armando Pombeiro, Marina Kirillova, Alexander Kirillov, José Armando Silva, João Fraústo Silva
  • Patent number: 7495130
    Abstract: A process for preparing mono- or poly-C1-C20-alkyl- and/or -halogen-substituted arylcarbonyl chlorides (I), by, in a first stage, reacting a mono- or poly-C1-C20-alkyl- and/or -halogen-substituted aromatic (II) with CCl4 in the presence of a Friedel-Crafts catalyst to give the corresponding mono- or poly-C1-C20-alkyl- and/or -halogen-substituted trichloromethylated aromatic (III), and, in a second stage, treating the trichloromethylated aromatic (III) with water or a protic acid in the presence of a catalyst to obtain the arylcarbonyl chloride (I). In a particularly preferred embodiment, the trichloromethylated aromatic (III) is not isolated as an intermediate and is used in the second stage dissolved in the solvent of the first stage.
    Type: Grant
    Filed: July 14, 2004
    Date of Patent: February 24, 2009
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Maase, Gerhard Bertlein, Holger Ganz, Matthias Dust
  • Patent number: 7435849
    Abstract: A process for the preparation of acid halides of formula I which are useful as intermediates in the preparation of i.a. pharmaceutically active compounds.
    Type: Grant
    Filed: October 17, 2006
    Date of Patent: October 14, 2008
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Ursula Hoffmann, Goesta Rimmler
  • Patent number: 7423174
    Abstract: The present invention provides a process for selectively separating HF and like acids present along with water-unstable organic acid fluorides. In particular, the invention provides a process for separating an acid from a system in which the acid and an organic acid fluoride are present, the organic acid fluoride being represented by formula (I): RCOF??(I) wherein R is a fluorine atom; a C1-20 linear, branched or cyclic alkyl or halogenated alkyl group that may contain a heteroatom; or a C6-20 aryl or halogenated aryl group that may contain a heteroatom; the process comprising using as a deacidifying agent an aromatic heterocyclic compound having a boiling point of at least 50° C. and having one or more nitrogen atoms as heteroatom.
    Type: Grant
    Filed: May 30, 2002
    Date of Patent: September 9, 2008
    Assignee: Daikin Industries, Ltd.
    Inventors: Masaki Irie, Masahiro Kondou
  • Patent number: 7405331
    Abstract: The process for producing a (fluoroalkyl)benzene derivative according to the present invention comprises a step of reducing the total content of group 3 to group 12 transition metals in an alkylbenzene derivative to 500 ppm or less in terms of metal atoms; a step of halogenating the branched alkyl group of the purified alkylbenzene derivative by a photohalogenation to obtain a (haloalkyl)benzene derivative; and a step of subjecting the (haloalkyl)benzene derivative to a halogen-fluorine exchange using HF in an amount of 10 mol or higher per one mole of the (haloalkyl)benzene derivative. The (fluoroalkyl)benzene derivative produced by the process is reduced in the content of impurities such as residual halogens and residual metals, and is useful as intermediates for functional chemical products for use in applications such as medicines and electronic materials.
    Type: Grant
    Filed: April 24, 2003
    Date of Patent: July 29, 2008
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Toshio Hidaka, Norio Fushimi, Takafumi Yoshimura, Takeshi Kawai
  • Patent number: 7375253
    Abstract: A process for the synthesis of (per)fluorinated mono-functional carbonyl compounds having the following formula (I): F-A-RF—B—C(O)X1??(I) wherein: X1=F, CF3; A, B equal to or different from each other, are independently (per)fluoroalkylene or (per)fluorooxyalkylene groups; RF is —ORf1O— wherein Rf1=perfluoroalkylene or —ORf2, wherein Rf2 is a perfluorooxyalkylene chain; said process comprising the following steps: A) obtainment of the formula (II) mono-hypofluorite: FO—CFX2-A-RF—B—C(O)X1??(II) by partial fluorination with elemental fluorine of the carbonyl groups of the formula (III) compound: X2(O)C-A-RF—B—C(O)X1??(III) in the presence of a formula MeFy catalyst, Me being an alkaline or alkaline-earth metal or Ag, y=1 or 2; B) thermal decomposition of the compound (II) to give the compounds according to the following scheme: FO—CFX2-A-RF—B—C(O)X1 (II) - - - ?F-A-RF—B—C(O)X1 (I)+(O)CFX2.
    Type: Grant
    Filed: January 9, 2004
    Date of Patent: May 20, 2008
    Assignee: Solvay Solexis S.p.A.
    Inventors: Giovanni Fontana, Walter Navarrini
  • Patent number: 7161030
    Abstract: Hydrofluoroethers of formula: T-CFX?—O—Rf—CFX-T???(II) wherein: T=CH3; X, X?, equal to or different from each other, are selected between F, CF3; T00?=F, Cl, H, C1–C3 perfluoroalkyl, CH3, CH2OH, COCl, CHO, CO2H; Rf is a perfluoroalkylene or a perfluoropolyoxyalkylene and respective preparation process by reduction with hydrogen in the presence of a platinum catalyst supported on metal fluorides of the corresponding compounds with at least one —COCl end group.
    Type: Grant
    Filed: July 31, 2003
    Date of Patent: January 9, 2007
    Assignee: Solvay Solexis S.p.A.
    Inventors: Rosaldo Picozzi, Antonella Di Meo, Claudio Tonelli
  • Patent number: 7141704
    Abstract: Process for obtaining hydrofluoroethers of formula (I): A-(Rf)n0—CF(Rf1)—O—Rh??(I) wherein a mono- or bifunctional carbonyl compound of formula (IV): B—Rf—C(O)Rf1??(IV) is reacted with at least one equivalent of a fluoroformate of formula (III) R—OC(O)F??(III) in the presence of an ion fluoride compound (catalyst) and of a dipolar aprotic organic compound, liquid and inert under the reaction conditions.
    Type: Grant
    Filed: March 26, 2004
    Date of Patent: November 28, 2006
    Assignee: Solvay Solexis S.P.A.
    Inventors: Walter Navarrini, Marco Galimberti, Giovanni Fontana
  • Patent number: 6911558
    Abstract: Describes a method for obtaining substantially pure chloromethyl chloroformate from a chloroformate mixture comprising chloromethyl chloroformate and methyl chloroformate by heating the chloroformate mixture in a reaction zone at temperatures ranging from at least 50° C. to the reflux temperature of the chloroformate mixture in the reaction zone while simultaneously removing volatile gaseous decomposition products from the reaction zone. Dichloromethyl chloroformate may also be present in the chloroformate mixture.
    Type: Grant
    Filed: February 5, 2003
    Date of Patent: June 28, 2005
    Assignee: PPG Industries Ohio, Inc.
    Inventors: Mark P. Bowman, Charles B. Kreutzberger
  • Patent number: 6605743
    Abstract: The invention relates to a continuous process for the preparation of pivaloyl chloride and of aroyl chloride, in particular of benzoyl chloride, which consists in reacting pivalic acid with a trichloromethylated aromatic compound in the presence of a catalyst at a temperature of between 60° C. and 180° C. under reduced pressure. The products formed are continuously removed from the reaction region, the hydrogen chloride formed being treated in a washing region in which a trichloromethylated compound moves countercurrentwise.
    Type: Grant
    Filed: December 23, 1998
    Date of Patent: August 12, 2003
    Assignee: Elf Atochem S.A.
    Inventors: Christophe Ruppin, Philippe Corbiere
  • Patent number: 6586626
    Abstract: The invention provides a process for producing a fluorine-containing compound from an inexpensive material. Namely, Compound I such as RACH2OH is reacted with Compound II such as XCORB to form Compound III such as RACH2OCORB, followed by fluorination in a liquid phase to form Compound IV such as RAFCF2OCORBF, which is converted to Compound V such as RAFCOF and/or Compound VI such as RBFCOF. RA is an alkyl group or the like, RB is a perhalogenoalkyl group or the like, RAF and RBF are fluorinated RA and RB, and X is halogen.
    Type: Grant
    Filed: September 24, 2001
    Date of Patent: July 1, 2003
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Shin Tatematsu, Hidenobu Murofushi
  • Publication number: 20010014759
    Abstract: 3,5-Bis(trifluoromethyl)benzoyl chlorides optionally substituted with fluorine or chlorine are advantageously prepared by converting 3,5-dimethylbenzoic acids optionally substituted with fluorine or chlorine into the corresponding acid chlorides; completely free-radically chlorinating said chlorides in the side chains, giving 3,5-bis(trichloromethyl)benzoyl chlorides optionally substituted by fluorine or chlorine; fluorinating the latter with anhydrous hydrogen fluoride and/or antimony pentafluoride, giving 3,5-bis(trifluoromethyl)benzoyl fluorides optionally substituted with fluorine or chlorine; and then reacting the 3,5-bis(trifluoromethyl)benzoyl fluorides with silicon tetrachloride in the presence of a further Lewis acid. Some of the 3,5-bis(trihalogenomethyl) and 3,5-dimethylbenzoyl halides which arise as intermediates are novel compounds.
    Type: Application
    Filed: January 25, 2001
    Publication date: August 16, 2001
    Inventors: Albrecht Marhold, Jorn Stolting
  • Patent number: 6262300
    Abstract: The present invention provides process for the preparation of chlorocarbonyl chlorides of the formula I R1—CHCl—Y—COCl  (I), where R1 is for example hydrogen or C1- to C20-alkyl and Y is for example a saturated or mono- or polyolefinically unsaturated C2-C8-alkylene chain, by reacting lactones with a chlorinating agent in the presence of a urea compound.
    Type: Grant
    Filed: April 20, 2000
    Date of Patent: July 17, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Jürgen Weyer, Armin Stamm, Theodor Weber, Jochem Henkelmann
  • Patent number: 6248919
    Abstract: A process for the preparation of preparation of farnesyltransferase inhibitors of formula (I) or pharmaceutically acceptable salts or prodrugs thereof, is disclosed.
    Type: Grant
    Filed: October 5, 1999
    Date of Patent: June 19, 2001
    Assignee: Abbott Laboratories
    Inventors: Todd S. McDermott, Anne E. Bailey, Ramiya Premchandran, Lakshima Bhagavatula
  • Patent number: 5912371
    Abstract: A method for preparing fatty acid chlorides. The method comprises reacting a silylation product of a fatty acid comprising at 1east 2 aliphatically unsaturated bonds per molecule and a chlorinating agent.
    Type: Grant
    Filed: October 27, 1997
    Date of Patent: June 15, 1999
    Assignee: Dow Corning Toray Silicone Co., Ltd.
    Inventors: Koji Nakanishi, Tadashi Okawa
  • Patent number: 5905169
    Abstract: A process is disclosed for preparing polyhaloacyl fluorides such as trifluoroacetyl fluoride and difluoroacetyl fluoride by oxidizing 1-chloro-1,2,2,2-trifluoroethanes and 1,1-dichloro-2,2-difluoroethane, respectively with oxygen.
    Type: Grant
    Filed: March 20, 1995
    Date of Patent: May 18, 1999
    Assignee: E. I. Du Pont De Nemours and Company
    Inventor: Stephen Ernest Jacobson
  • Patent number: 5869735
    Abstract: Process for the preparation of alkyl aryl ethers containing carboxyl groups which are suitable for the preparation of colour film couplers, or derivatives thereof, by reaction of aromatic alcohols with alkyl halides containing carboxyl groups or derivatives thereof and basic alkali metal or alkaline earth metal compounds, characterized in that the reaction is carried out in the melt of the aromatic alcohol.
    Type: Grant
    Filed: October 11, 1996
    Date of Patent: February 9, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Stefan Antons, Erich Hammerschmidt, Heinz Ulrich Blank, Helmut Fiege, Heinz-Gerd Hartges
  • Patent number: 5430186
    Abstract: A process for the continuous manufacture of carboxylic chlorides (I) of the general formula R-COCl, in which R stands for a C-organic radical containing from 1 to 30 C atoms, by the reaction of a carboxylic acid (II) with a reaction product (III) of phosgene (IV) and an N,N-substituted formamide (V), in which compounds II and III are passed in parallel flow upwardly into a zone, filled with compound III, in a reactor (1), the reaction mixture is allowed to rise in predominantly laminar flow, such that phase separation occurs to give a top I-phase and a bottom phase III' mainly comprising compound III and formamide formed and compound I is removed from the top phase and also portions of the bottom phase III' are removed at the rate at which they are formed.
    Type: Grant
    Filed: July 14, 1994
    Date of Patent: July 4, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Ksoll, Wolfgang Reuther, Roland Ettl
  • Patent number: 5362909
    Abstract: 2,4,5-Trihalogenobenzene derivatives of the formula ##STR1## in which R is --COOH, --COCl, --COF, --CN, --CONH.sub.2, --CH.sub.2 OH, --CH.sub.2 Cl, --CHCl.sub.2, --CCl.sub.3 or --CHO,R.sup.1 is H, Cl or F, andR.sup.2 is Cl or F,it only being possible for R.sup.1 or R.sup.2 to be F, and processes for their preparation starting from benzonitriles reacted with potassium fluoride. The novel compounds are intermediates for antibacterials such as quinolone carboxylic acids.
    Type: Grant
    Filed: October 29, 1992
    Date of Patent: November 8, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Erich Klauke, Uwe Petersen, Klaus Grohe
  • Patent number: 5296640
    Abstract: A process for preparing perhaloacyl chlorides such as trifluoroacetyl chloride by oxidizing lower perfluoroalkyl and monochloroperfluoroalkyl dichloromethane within the supercritical region and in the absence of water.
    Type: Grant
    Filed: September 15, 1992
    Date of Patent: March 22, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Stephen E. Jacobson, Wayne B. Ely
  • Patent number: 5278328
    Abstract: Disclosed is a process for producing a carboxylic acid chloride by reacting phosgene with a carboxylic acid or an anhydride thereof, which comprises effecting the reaction in the presence of a homopolymer or copolymer of a monomer represented by formula (I) or (II) below, a copolymer of the monomers represented by formulae (I) and (II) below, or a copolymer of at least one monomer selected from the group sensisting of the monomers represented by formulae (I) and (II) below with another monomer copolymerizable therewith:CH.sub.2 .dbd.CHNR.sup.1 COR.sup.2 (I)CH.sub.2 .dbd.CR.sup.3 CONR.sup.4 R.sup.5 (II).In these formulae R.sup.1, R.sup.2, and R.sup.4 each represents an alkyl group containing from 1 to 3 carbon atoms, or an alkylene group containing from 3 to 5 carbon atoms provided that R.sup.1 with R.sup.2, and R.sup.4 with R.sup.5 may each combine to form a ring structure through >N--CO-- or >N-- in the molecule; R.sup.3 and R.sup.
    Type: Grant
    Filed: March 11, 1992
    Date of Patent: January 11, 1994
    Assignee: Nippon Oil & Fats Co., Ltd.
    Inventors: Takeshi Endo, Toshikazu Takata, Shinichi Ohno, Fujio Takahashi
  • Patent number: 5258547
    Abstract: A process for preparing halogenated compounds of formula RCY(Z)CH.sub.2 CH(X)C(CH.sub.3)CH.sub.2 COR.sup.1 where X, Y and Z are halo, R is alkyl, halo, haloalkyl or aryl, and R.sup.1 is hydroxy, halo, alkoxy, alkyl or haloalkyl, or the residue of a pyrethroidal alcohol, in which a compound of formula CH.sub.2 =CHC(CH.sub.3).sub.2 COR.sup.1 is reacted with a sulphonyl halide of formula RCY(Z)SO.sub.2 X. The process avoids the use of volatile halocarbons in the production of valuable intermediates for insecticides.
    Type: Grant
    Filed: January 9, 1992
    Date of Patent: November 2, 1993
    Assignee: Imperial Chemical Industries plc
    Inventor: Gary N. Sheldrake
  • Patent number: 5247105
    Abstract: The invention provides a process for preparing fatty acid halide by reacting a fatty acid with a halogenating agent optionally followed by hydrolysis of unreacted halogenating agent and separating the fatty acid halide upper layer from the inorganic lower layer characterized in that a fatty acid nitrogen derivative, preferably a fatty amide has been incorporated in the reaction mixture. Preferably the fatty acid is a saturated or unsaturated C.sub.6 to C.sub.24 fatty acid and the halogenating agent a phosphorus halide, especially phosphorus trichloride.
    Type: Grant
    Filed: February 26, 1991
    Date of Patent: September 21, 1993
    Assignee: Unilever Patent Holdings B.V.
    Inventors: Reginald D. O. Evans, Raymond Jennings
  • Patent number: 5155234
    Abstract: A process for the preparation of nitrophthalic acid by the nitration of phthalic acid and/or phthalic anhydride using only nitric acid, said nitric acid having a concentration of at least about 95% by weight, and then recovering the nitrophthalic acid formed from the nitric acid solution.
    Type: Grant
    Filed: May 13, 1991
    Date of Patent: October 13, 1992
    Assignee: General Electric Company
    Inventor: Roy R. Odle
  • Patent number: 5130477
    Abstract: A novel oligohexafluoropropylene oxide derivative is a useful intermediate. It is prepared by reacting an oligohexafluoropropylene oxide carbonyl fluoride with a metal iodide.
    Type: Grant
    Filed: August 22, 1991
    Date of Patent: July 14, 1992
    Assignee: Shin-Etsu Chemical Company Limited
    Inventors: Noriyuki Koike, Masayuki Oyama, Toshio Takago
  • Patent number: 5113016
    Abstract: Excess terephthalic acid or isophthalic acid is reacted with a phosgene/DMF complex nearly to completion in one or more stages to form terephthaloyl chloride or isophthaloyl chloride; in another stage, by-product formylbenzoyl chloride is oxidized and terephthaloyl chloride or isophthaloyl chloride containing less than 100 ppm of formylbenzoyl chloride and/or dichlorotoluoylchloride is recovered.
    Type: Grant
    Filed: August 20, 1990
    Date of Patent: May 12, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Robert L. Seagraves
  • Patent number: 4954651
    Abstract: Trans-2,2-dimethyl-3-(2,2-dihalovinyl)-cyclopropane carboxylic acid halides which are an intermediate for insecticides are prepared by allowing arylphosphines to react with cis- or cis-/trans-mixed 2,2-dimethyl-3-(2,2-dihalovinyl)-cyclopropane carboxylic acid halides of the formula ##STR1## wherein both X and Y are halogen atoms, respectively, at a temperature of -10.degree. to 100.degree. C., in the presence of absence of halogen compounds.
    Type: Grant
    Filed: May 1, 1989
    Date of Patent: September 4, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Gohfu Suzukamo, Yoji Sakito, Masami Fukao, Koji Hagiya
  • Patent number: 4874473
    Abstract: Diastereomers can be separated with good industrial success with the aid of extractive distillation. The separation process is characterized in that an auxiliary which changes the partial pressure of the various diastereomers to be separated to a different degree and thus allows easier separation of the diastereomers by distillation is added during the distillation. Using the present process diastereomic cis/trans-permetric acid methyl esters and mixtures of menthol and isomenthol can be separated with isolation of 99% pure product.
    Type: Grant
    Filed: April 16, 1987
    Date of Patent: October 17, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dieter Arlt, Ulrich Schwartz, Hans-Walter Brandt, Wolfgang Arlt, Andreas Nickel